反应详情

A solution of silver perchlorate (4.75 g, 23 mmol) in water (10 mL) was added to a solution of 4-bromomethyl-2,1,3-benzothiadiazole (4.38 g, 19 mmol) in 1,4-dioxane. The mixture was refluxed for 4 hours to afford a light-yellow suspension. After cooling to room temperature, the precipitate was filtered off through a pad of celite and washed with CH2Cl2. The filtrate was washed with water and brine, dried over Na2SO4. Concentration using a rotary evaporator and subsequent column chromatography on silica gel using hexane/ethyl acetate (5:1) as the eluent afforded 4-hydroxymethyl-2,1,3-benzothiadiazole (2.0 g, 63%) as a light-yellow solid. Rf=0.23 (hexane/ethyl acetate=5:1); 1H NMR (200 MHz, CDCl3) δ2.73 (t,J=6.4 Hz, 1H), 5.18 (d,J=6.4 Hz, 2H), 7.58 (m, 2H), 7.94 (m, 1H); HRMS:Calcd. for C7H6N2OS 166.0201, found 166.0219.

1. temperatureThe mixture was refluxed for 4 hours
2. customto afford a light-yellow suspension
3. filtrationthe precipitate was filtered off through a pad of celite
4. washwashed with CH2Cl2
5. washThe filtrate was washed with water and brine
6. dry with materialdried over Na2SO4
7. concentrationConcentration
8. customa rotary evaporator and subsequent column chromatography on silica gel